Sodium Hydroxide → HCID 59020336, compound

Participants

Reaction Steps

A solution of 70 mg (0.16 mmol) of N-[3-(5-bromo-2-chloro-pyrimidin-4-yloxy)-propyl]-3-nitro-benzenesulfonamide in 5 ml of THF is mixed at 0° C. with 1.0 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 2 hours, the reaction solution is mixed again with 0.2 ml of Ti(III)Cl solution and stirred for another hour. The batch is made basic with 1N NaOH solution and then filtered. The filter cake is rewashed 2× in each case with 50 ml of ethyl acetate/MeOH (30 ml/20 ml). The filtrate is concentrated by evaporation in a rotary evaporator and then extracted with ethyl acetate (2×). The combined organic phases are washed with NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 1:1, Flashmaster II). 32 mg (0.08 mmol, corresponding to 49% of theory) of the product is obtained.

Provenance & Evidence